#15 BOH

SYNTHESIS: To a solution of 30 g piperonal in 100 mL acetic acid there
was added 20 mL nitromethane and 10 mL cyclohexylamine. After heating
on the steam bath for 1.5 h, the reaction mixture started to
crystallize. The mixture was cooled in an ice bath, and the heavy
mass of deposited crystals removed by filtration and washed with 20 mL
acetic acid. All was supended in 100 mL warm MeOH, cooled again, and
filtered to give 24.5 g of 3,4-methylenedioxy-beta-nitrostyrene as
canary-yellow crystals, with a mp of 158-160 °C. Reduction of this
compound with LAH gives rise to MDPEA, which is a separate entry with
a recipe of its own.

To a vigorously stirred suspension of 20 g 3,4-methylenedioxy-beta-nitro
-styrene in 100 mL anhydrous MeOH there was added a freshly prepared
solution of 5.5 g elemental sodium in 100 mL MeOH. The nitrostyrene
goes into solution over the course of 5 min. There was then added,
first, 50 mL acetic acid with the stirring continued for an additional
1 min. There was then added 300 mL H2O. An oil separated and was
extracted into 200 mL CH2Cl2. The organic extract was washed with 500
mL dilute aqueous NaHCO3, followed by 500 mL H2O. Removal of the
solvent gave a residue that was distilled at 128-145 °C at 0.4 mm/Hg,
providing 16.6 g of a yellow viscous liquid which slowly crystallized.
An analytical sample was recrystallized from four volumes of MeOH to
give 1-methoxy-1-(3,4-methylenedioxyphenyl)-2-nitroethane as bright
yellow crystals with a mp of 58-59 °C. Anal. (C10H11NO5) C,H.

A solution of LAH (100 mL of 1 M solution in THF) was cooled, under
He, to 0 °C with an external ice bath. With good stirring there was
added 2.5 mL 100% H2SO4 dropwise, to minimize charring. This was
followed by the addition of 12 g
1-methoxy-1-(3,4-methylenedioxyphenyl)-2-nitroethane over the course
of 2 min. There was an immediate loss of color. After a few minutes
further stirring, the temperature was brought up to a reflux with a
heating mantle. There was a gentle gas evolution for a few min,
followed by an exothermic reaction that exceeded the capacity of the
condenser. Once the reaction had subsided, the unreacted hydride was
destroyed with a minimum of IPA, and 15% NaOH was added to convert the
inorganics to a loose white filterable mass. The reaction mixture was
filtered, and the filter cake washed thoroughly with THF. The
combined filtrate and washes were stripped of solvent under vacuum,
providing an orange oil. This was dissolved in 400 mL dilute H2SO4,
which was washed with 3x75 mL CH2Cl2. After making the aqueous phase
basic, it was extracted with 2x100 mL CH2Cl2. The pooled extracts
were stripped of solvent under vacuum, and the residue distilled at
103-112 °C at 0.5 mm/Hg. There was obtained 2.5 g of a colorless,
viscous oil which was dissolved in 25 mL IPA, neutralized with 45
drops of concentrated HCl, and finally diluted with 30 mL anhydrous
Et2O. There was thus formed
beta-methoxy-3,4-methylenedioxyphenethylamine hydrochloride (BOH) as a
fine white crystalline product. The mp was 105-106.5 °C, with
bubbling and darkening. The mp properties proved to be inconsistent,
as the salt was a hydrate. Recrystallization from CH3CN, or simply
heating to 100 °C in toluene, converted the salt to an anhydrous form,
with mp of 152-153 °C. Anal. (C10H14ClNO3) C,H.

DOSAGE: 80 - 120 mg.

DURATION: 6 - 8 h.

QUALITATIVE COMMENTS: (with 90 mg) Distinct body awareness in an
hour. The threshold is mostly physical. Faint sense of inside
warmth, skin prickling, cold feet, loose bowels, anorexia. By the
fifth hour, I was on the downslope, and in retrospect I found it good
humored but not insightful.

(with 100 mg) There was a vague nausea, and a chilling of the feet.
It reached a real plus two, with dilated pupils and quite a thirst.
How can one describe the state? There were no visuals, and I was not
even stoned. I was just very turned on. And I was completely back to
baseline by hour number six.

EXTENSIONS AND COMMENTARY: There are several reports of a nice, mild
mood enhancement in the 20-40 milligram dosage area, but searches for
psychedelic effects at higher levels gave a strange mix of some sort
of an altered state along with bodily discomfort. The BOH name for
this member of the BOX family follows the convention discussed in the
BOD recipe--with RHS for homopiperonylamine, the simplest of the
muni-metro family, q.v. The demethylated homologue of BOH is BOHH,
and is the methylenedioxy analogue of norepinephrine. It might well
hydrolytically open up in the body to provide this neurotransmitter,
and serve as some sort of transmitter in its own right. It is
discussed under DME.

Maybe there is something to the concept that when you imitate a
neurotransmitter too closely, you get a hybrid gemisch of activity.
The term "pro-drug" is used to identify a compound that may not be
intrinsically active, but one which metabolizes in the body to provide
an active drug. I feel the term should have been pre-drug, but
pro-drug was the word that caught on. BOH may well act in the body as
a pro-drug to norepinephrine, but with the temporary blocking of the
polar functions with ether groups, it can gain access to the brain.
And once there, it can be stripped of these shields and play a direct
neurological role. I uncovered a very similar analogy in the
tryptamine world some years ago. Just as norepinephrine is a
neurotransmitter, so is serotonin. And I found that by putting an
O-ether on the indolic phenol (to hide its polarity) and an
alpha-methyl group next to the primary amine (to protect it from
metabolic deaminase), it became an extremely potent, and most complex,
psychedelic. This was the compound alpha,O-dimethylserotonin, or
a,O-DMS. There is an uncanny analogy between this tryptamine and the
phenethylamine BOH.

Somehow the quiet voice deep inside me says, don't use too much, too
quickly. Maybe one of the optical isomers is the body thing, and the
other isomer is the mind thing. So far, only the racemic mixture has
been tasted, to the best of my knowledge.